3-(Trifluoromethyl)phenol → HCID 66653794、化合物

HRID 571777ノート

反応式

HRID 571777 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:30])[F:31])[CH:24]=3)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 73763-(Trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

生成物 1

HCID 66653794HCID 66653794、化合物収率 47.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

実験手順

A mixture of 4-benzyl-2-(4-bromo-phenyl)-morpholine (1.5 g, 4.6 mmol), 3-(trifluoromethyl)phenol (0.83 mL, 6.8 mmol), copper(I) iodide (438 mg, 2.3 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.48 mL, 2.3 mmol), and cesium carbonate (2.96 g, 9.1 mmol), in toluene (20 mL) was heated under reflux for 3 days. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The layers were separated. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:heptanes 5:95) to afford 4-benzyl-2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-morpholine (0.9 g), which was used as such in the next step.

後処理

  1. temperatureunder reflux for 3 days
  2. customthe mixture was partitioned between EtOAc and water
  3. customThe layers were separated
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (EtOAc:heptanes 5:95)

出典と根拠

ORDレコード
ord-2d3fe959161544b0b3261af5f0a23a7f
出典データセット
uspto-grants-2015_05
特許番号
US09029371B2

反応ノート

読み込み中…